European Patent Application (EP-A) No. 83,975 (published July 20, 1983) discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Q is selected from various five or six-membered aromatic or partially unsaturated heterocyclic rings containing 2 or 3 heteroatoms selected from O, S or NR.
EP-A-85,476 (published Aug. 10, 1983) discloses herbicidal benzenesulfonamides of formulae ##STR2## wherein Q is selected from various 5-membered aromatic heterocycles, and their dihydro and tetrahydro analogs, which contain one heteroatom selected from O, S or NR, or Q is a saturated or partially unsaturated 6-membered ring containing one heteroatom selected from O or S; and
Q.sup.1 is a 6-membered aromatic heterocycle containing one to three N atoms. PA1 B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, CO.sub.2 R, etc.; and PA1 D is H or C.sub.1 -C.sub.8 alkyl. PA1 Q is an unsubstituted or substituted five-membered heterocyclic radical which is bound by way of a carbon atom and which contains 2 or 3 identical or different heteroatoms. p Unexamined Japanese Patent Application No. 9,013,778 (priority July 15, 1982) filed by Nihon Noyaku describes herbicidal pyrazolesulfonamides with halo, alkyl and alkoxycarbonyl substituents. PA1 C is --CO--, CR.sub.21 R.sub.22 or --SO.sub.2 --; and PA1 n is 0 or 1. PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, amino, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sup.III, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, CH.sub.2 CN, CH.sub.2 OCH.sub.3, or CH.sub.2 SCH.sub.3 ; PA1 R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 M is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, phenyl, phenyl substituted with Cl, NO.sub.2, CH.sub.3 or OCH.sub.3, C.sub.2 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 alkylsulfonyl or SO.sub.2 NR.sub.4 R.sub.5 ; ##STR10## G is C.dbd.O or SO.sub.2 ; W is O, S, CHR.sub.2 or NR.sub.3 ; PA1 W.sub.2 is O, S, SO.sub.2, CHR.sub.2 or NR.sub.3 ; PA1 R.sub.2 is H, C.sub.1 -C.sub.2 alkyl, Cl, F, or Br; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA1 E and E.sub.1 are independently C.sub.3 -C.sub.4 alkylene, C.sub.3 -C.sub.4 alkenylene or C.sub.4 alkenyldienyl; PA1 E.sub.2 and E.sub.4 are independently C.sub.1 -C.sub.2 alkylene or C.sub.2 alkenylene; PA1 E.sub.3 and E.sub.5 independently are C.sub.2 -C.sub.3 alkylene or C.sub.2 -C.sub.3 alkenylene; and PA1 E, E.sub.1, E.sub.2, E.sub.3, E.sub.4 and E.sub.5 may optionally be substituted by 1-4 groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkenyl, OH, halogen or C.sub.1 -C.sub.4 haloalkoxy; further, when W is O, CHR.sub.2 or NR.sub.3, one of the carbon atoms of E may be in the form of a carbonyl group, and when W.sub.2 is O, CHR.sub.2 or NR.sub.3, one of the carbon atoms of E.sub.4 or E.sub.5 may be in the form of a carbonyl group, provided that said carbonyl groups are not bonded directly to G; ##STR11## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C(O)R.sub.6, ##STR12## m is 2 or 3; L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.6 is H or CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; and PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 a. when G is SO.sub.2, then W is O, CHR.sub.2 or NR.sub.3 ; PA1 b. when E.sub.2 or E.sub.4 is C.sub.2 alkylene or C.sub.2 alkenylene then E.sub.3 or E.sub.5 is C.sub.2 alkylene or C.sub.2 alkenylene; PA1 c. when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 d. when M is other than H, alkyl, alkenyl, alkynyl or phenyl, optionally substituted, then R.sub.1 is H, alkyl, haloalkyl or halogen; PA1 e. when X or Y is OCF.sub.2 H, then Z is CH; PA1 f. when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 is less than or equal to two and the number of carbons of Q is less than or equal to eight; and PA1 g. when W.sub.1 is S, then R is H, A is A-1, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR13## PA1 1. Compounds of Formula I where PA1 2. Compounds of Preferred 1 where PA1 4. Compounds of Preferred 2 where Q is Q.sub.2 ; PA1 5. Compounds of Preferred 2 where Q is Q.sub.3 ; PA1 6. Compounds of Preferred 2 where Q is Q.sub.4 ; PA1 7. Compounds of Preferred 2 where Q is ##STR15## R.sub.7, R.sub.8, R.sub.10 are independently H or CH.sub.3 ; and R.sub.11 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 8. Compounds of Preferred 7 where PA1 9. Compounds of Preferred 8 where PA1 10. Compounds of Preferred 9 where PA1 11. Compounds of Preferred 10 where Q is Q-1; PA1 12. Compounds of Preferred 10 where Q is Q-2; PA1 13. Compounds of Preferred 10 where Q is Q-3; PA1 14. Compounds of Preferred 10 where Q is Q-4; PA1 15. Compounds of Preferred 10 where Q is Q-5; PA1 16. Compounds of Preferred 10 where Q is Q-6; PA1 17. Compounds of Preferred 10 where Q is Q-7; PA1 18. Compounds of Preferred 10 where Q is Q-8; PA1 19. Compounds of Preferred 10 where Q is Q-9; PA1 20. Compounds of Preferred 10 where Q is Q-10; PA1 21. Compounds of Preferred 10 where Q is Q-11; PA1 22. Compounds of Preferred 10 where Q is Q-12; PA1 23. Compounds of Preferred 10 where Q is Q-13; PA1 24. Compounds of Preferred 10 where Q is Q-14; PA1 25. Compounds of Preferred 10 where Q is Q-15; PA1 26. Compounds of Preferred 10 where Q is Q-16; PA1 27. Compounds of Preferred 10 where Q is Q-17; PA1 28. Compounds of Preferred 10 where Q is Q-18; PA1 29. Compounds of Preferred 10 where Q is Q-19; PA1 30. Compounds of Preferred 10 where Q is Q-20; PA1 31. Compounds of Preferred 10 where Q is Q-21; PA1 32. Compounds of Preferred 10 where Q is Q-22; PA1 33. Compounds of Preferred 10 where Q is Q-23; PA1 34. Compounds of Preferred 10 where Q is Q-24; PA1 35. Compounds of Preferred 10 where Q is Q-25; PA1 36. Compounds of Preferred 10 where Q is Q-26; PA1 37. Compounds of Preferred 10 where Q is Q-27; PA1 38. Compounds of Preferred 10 where Q is Q-28; PA1 39. Compounds of Preferred 10 where Q is Q-29; PA1 40. Compounds of Preferred 10 where Q is Q-30; PA1 41. Compounds of Preferred 10 where Q is Q-31; PA1 42. Compounds of Preferred 10 where Q is Q-32; PA1 43. Compounds of Preferred 10 where Q is Q-33; PA1 44. Compounds of Preferred 10 where Q is Q-34; PA1 45. Compounds of Preferred 10 where Q is Q-35; PA1 46. Compounds of Preferred 10 where Q is Q-36; PA1 47. Compounds of Preferred 10 where Q is Q-37; PA1 48. Compounds of Preferred 10 where Q is Q-38; PA1 49. Compounds of Preferred 10 where Q is Q-39; PA1 50. Compounds of Preferred 10 where Q is Q-40; PA1 51. Compounds of Preferred 10 where Q is Q-41; PA1 52. Compounds of Preferred 10 where Q is Q-42; PA1 53. Compounds of Preferred 10 where Q is Q-43; PA1 54. Compounds of Preferred 10 where Q is Q-44; PA1 55. Compounds of Preferred 10 where Q is Q-45; PA1 56. Compounds of Preferred 10 where Q is Q-46; PA1 57. Compounds of Preferred 10 where Q is Q-47; PA1 58. Compounds of Preferred 10 where Q is Q-48; PA1 59. Compounds of Preferred 10 where Q is Q-49; PA1 60. Compounds of Preferred 10 where Q is Q-50; PA1 61. Compounds of Preferred 10 where Q is Q-51; PA1 62. Compounds of Preferred 10 where Q is Q-52; PA1 63. Compounds of Preferred 10 where Q is Q-53; PA1 64. Compounds of Preferred 10 where Q is Q-54; PA1 65. Compounds of Preferred 10 where Q is Q-55; PA1 66. Compounds of Preferred 10 where Q is Q-56; PA1 67. Compounds of Preferred 10 where Q is Q-57; PA1 68. Compounds of Preferred 10 where Q is Q-58; PA1 69. Compounds of Preferred 10 where Q is Q-59; PA1 70. Compounds of Preferred 10 where Q is Q-60; PA1 71. Compounds of Preferred 10 where Q is Q-61; PA1 72. Compounds of Preferred 10 where Q is Q-62; PA1 73. Compounds of Preferred 10 where Q is Q-63; PA1 74. Compounds of Preferred 10 where Q is Q-64; PA1 75. Compounds of Preferred 10 where Q is Q-65; PA1 76. Compounds of Preferred 10 where Q is Q-66; PA1 77. Compounds of Preferred 10 where Q is Q-67; PA1 78. Compounds of Preferred 10 where Q is Q-68; PA1 79. Compounds of Preferred 10 where Q is Q-69; PA1 80. Compounds of Preferred 10 where Q is Q-70; PA1 81. Compounds of Preferred 10 where Q is Q-71; PA1 82. Compounds of Preferred 10 where Q is Q-72; PA1 83. Compounds of Preferred 10 where Q is Q-73; PA1 84. Compounds of Preferred 10 where Q is Q-74; PA1 85. Compounds of Preferred 10 where Q is Q-75; PA1 86. Compounds of Preferred 10 where Q is Q-76; PA1 87. Compounds of Preferred 10 where Q is Q-77; PA1 88. Compounds of Preferred 10 where Q is Q-78; PA1 89. Compounds of Preferred 10 where Q is Q-79; PA1 90. Compounds of Preferred 10 where Q is Q-80; PA1 91. Compounds of Preferred 10 where Q is Q-81; PA1 92. Compounds of Preferred 10 where Q is Q-82; PA1 93. Compounds of Preferred 10 where Q is Q-83; PA1 94. Compounds of Preferred 10 where Q is Q-84; PA1 95. Compounds of Preferred 10 where Q is Q-85; PA1 96. Compounds of Preferred 10 where Q is Q-86; PA1 97. Compounds of Preferred 10 where Q is Q-87; PA1 98. Compounds of Preferred 10 where Q is Q-88; PA1 99. Compounds of Preferred 10 where Q is Q-89; PA1 100. Compounds of Preferred 10 where Q is Q-90; PA1 101. Compounds of Preferred 10 where Q is Q-91; PA1 102. Compounds of Preferred 10 where Q is Q-92; PA1 103. Compounds of Preferred 10 where Q is Q-93; PA1 104. Compounds of Preferred 10 where Q is Q-94; PA1 105. Compounds of Preferred 10 where Q is Q-95; PA1 106. Compounds of Preferred 10 where Q is Q-96; PA1 107. Compounds of Preferred 10 where Q is Q-97; PA1 108. Compounds of Preferred 10 where Q is Q-98; PA1 109. Compounds of Preferred 10 where Q is Q-99; PA1 110. Compounds of Preferred 10 where Q is Q-100; PA1 111. Compounds of Preferred 10 where Q is Q-101; PA1 112. Compounds of Preferred 10 where Q is Q-102; PA1 113. Compounds of Preferred 10 where Q is Q-103; PA1 114. Compounds of Preferred 10 where Q is Q-104; PA1 115. Compounds of Preferred 10 where Q is Q-105; PA1 116. Compounds of Preferred 10 where Q is Q-106; PA1 117. Compounds of Preferred 10 where Q is Q-107; PA1 118. Compounds of Preferred 10 where Q is Q-108; PA1 119. Compounds of Preferred 10 where Q is Q-109; PA1 120. Compounds of Preferred 10 where Q is Q-110; PA1 121. Compounds of Preferred 10 where Q is Q-111; PA1 122. Compounds of Preferred 10 where Q is Q-112; PA1 123. Compounds of Preferred 10 where Q is Q-113; PA1 124. Compounds of Preferred 10 where Q is Q-114; PA1 125. Compounds of Preferred 10 where Q is Q-115; PA1 126. Compounds of Preferred 10 where Q is Q-116; PA1 127. Compounds of Preferred 10 where Q is Q-117; PA1 128. Compounds of Preferred 10 where Q is Q-118; PA1 129. Compounds of Preferred 10 where Q is Q-119; PA1 130. Compounds of Preferred 10 where Q is Q-120; PA1 131. Compounds of Preferred 10 where Q is Q-121; PA1 132. Compounds of Preferred 10 where Q is Q-122; PA1 133. Compounds of Preferred 10 where Q is Q-123; PA1 134. Compounds of Preferred 10 where Q is Q-124; PA1 135. Compounds of Preferred 10 where Q is Q-125; PA1 136. Compounds of Preferred 10 where Q is Q-126; PA1 137. Compounds of Preferred 10 where Q is Q-127; PA1 138. Compounds of Preferred 10 where Q is Q-128; PA1 139. Compounds of Preferred 10 where Q is Q-129; PA1 140. Compounds of Preferred 10 where Q is Q-130; PA1 141. Compounds of Preferred 10 where Q is Q-131; PA1 142. Compounds of Preferred 10 where Q is Q-132; PA1 143. Compounds of Preferred 10 where Q is Q-133; PA1 144. Compounds of Preferred 10 where Q is Q-134; PA1 145. Compounds of Preferred 10 where Q is Q-135; PA1 146. Compounds of Preferred 10 where Q is Q-136; PA1 147. Compounds of Preferred 10 where Q is Q-137; PA1 148. Compounds of Preferred 10 where Q is Q-138; PA1 149. Compounds of Preferred 10 where Q is Q-139; PA1 150. Compounds of Preferred 10 where Q is Q-140; PA1 151. Compounds of Preferred 10 where Q is Q-141; PA1 152. Compounds of Preferred 10 where Q is Q-142; PA1 153. Compounds of Preferred 10 where Q is Q-143; PA1 154. Compounds of Preferred 10 where Q is Q-144; PA1 155. Compounds of Preferred 10 where Q is Q-145; PA1 156. Compounds of Preferred 10 where Q is Q-146; PA1 157. Compounds of Preferred 10 where Q is Q-147; PA1 158. Compounds of Preferred 10 where Q is Q-148; PA1 159. Compounds of Preferred 10 where Q is Q-149; PA1 160. Compounds of Preferred 10 where Q is Q-150; PA1 161. Compounds of Preferred 10 where Q is Q-151; PA1 162. Compounds of Preferred 10 where Q is Q-152; PA1 163. Compounds of Preferred 10 where Q is Q-153; PA1 164. Compounds of Preferred 10 where Q is Q-154; PA1 165. Compounds of Preferred 10 where Q is Q-155; PA1 166. Compounds of Preferred 10 where Q is Q-156; PA1 167. Compounds of Preferred 10 where Q is Q-157; PA1 168. Compounds of Preferred 10 where Q is Q-158; PA1 169. Compounds of Preferred 10 where Q is Q-159; PA1 170. Compounds of Preferred 10 where Q is Q-160; PA1 171. Compounds of Preferred 10 where Q is Q-161; PA1 172. Compounds of Preferred 10 where Q is Q-162; PA1 173. Compounds of Preferred 10 where Q is Q-163; PA1 174. Compounds of Preferred 10 where Q is Q-164; PA1 175. Compounds of Preferred 10 where Q is Q-165; PA1 176. Compounds of Preferred 10 where Q is Q-166. PA1 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(tetrahydro-2-oxo furan-3-yl)pyrazole-3-sulfonamide; PA1 N-[(4-methoxy-6-methyltriazin-2-yl)aminocarbonyl]-1-methyl-4-(tetrahydro-2- oxofuran-3-yl)pyrazole-3-sulfonamide; and PA1 N-[4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(3-oxo-1-cyclohexe nyl)-1H-pyrazole-5-sulfonamide, m.p. 175.degree.-182.degree. C. (dec). PA1 K is CO.sub.2 CH.sub.3, NHCOCH.sub.3 or H, and PA1 K.sub.1 is COOH, NH.sub.2 or H. PA1 K is NHCOCH.sub.3 ; and PA1 K.sub.1 is NH.sub.2. PA1 K is Br, H, or SR.sub.12, R.sub.12 is C.sub.2 -C.sub.4 alkyl or benzyl, and P is an appropriate alcohol protecting group such as CH.sub.2 Ph, t-butyl, Si(CH.sub.3).sub.2 (t-Bu), etc. PA1 K is Br, H, or SR.sub.12, R.sub.12 is C.sub.2 -C.sub.4 alkyl or benzyl, and P is a protecting group as defined above in Equation 44.
South African Patent Application No. 83/8416 (published May, 1984) discloses herbicidal benzenesulfonamides of formula ##STR3## wherein A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms.
No. EP-A-95,925 (published Dec. 7, 1983) discloses herbicidal pyrazolesulfonamides in which the group adjacent to the sulfonamide moiety may be selected from H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.23, S(O).sub.n R.sub.24 or SO.sub.2 NR.sub.19 R.sub.20.
No. EP-A-87,780 (published Sept. 7, 1983) claims pyrazole sulfonamides of general formula ##STR4## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
No. EP-A-96,003 (published Nov. 28, 1983) discloses herbicidal compounds of general formula ##STR5## wherein R.sub.1 is H or C.sub.1 -C.sub.3 alkyl; and
European Publication No. 116,518 (published 8/22/84; Swiss priority 2/4/83) discloses herbicidal sulfonylureas of the formula ##STR6## where, in part, X is --NR.sub.6 R.sub.7, --N(SO.sub.2 R.sub.9).sub.2 or ##STR7## A is --CO--, --SO.sub.2 --, --CONR.sub.23 -- or --CO.sub.2 --; B is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene;